Propene is treated with BH3 in THF and then H2O2/NaOH to give A. A is oxidised with PCC to B. B is treated with CH3MgBr followed by H3O+ to give C. C is treated with excess I2/NaOH, giving a yellow precipitate and an organic salt D. D is

JEE Advanced levelSingle correct optionDifficulty 3 of 3ap071

Propene is treated with $BH X_{3}$ in THF and then $H X_{2} O X_{2}$ / $NaOH$ to give A. A is oxidised with $PCC$ to B. B is treated with $CH X_{3} MgBr$ followed by $H X_{3} O X^{+}$ to give C. C is treated with excess $I X_{2}$ / $NaOH$ , giving a yellow precipitate and an organic salt D. D is

Hydroboration-oxidation gives anti-Markovnikov propan-1-ol (A). PCC gives propanal (B), and

CH X_{3} MgBr

adds to the aldehyde to give the secondary alcohol butan-2-ol (C). Hypoiodite oxidises C to butanone, which is cleaved by the haloform reaction into

CHI X_{3}

and

CH X_{3} CH X_{2} COONa

, sodium propanoate.